Quagmire's Perfect Woman
by impossible.girl.21
Summary: Glenn Quagmire's determination to find a woman that will help him fulfill his sexual desires leads him to a young and vulnerable girl. They help each other bring their fantasies to life and explore the true pleasures of sex. Still in progress and more to come soon.
1. Chapter 1 -- The Dream

The sun was rising as Glenn Quagmire walked his latest conquest to his front door. "Thanks for such a great night, Glenn" she said almost convincingly.

"Anytime Darlene" he responded callously.

"It's Charlene, you jerk!" Those were the last words they shared before she stormed off, and left the Spooner Street residence. Her offence didn't faze Quagmire in the least. After all, it was a typical hook-up for him, and nothing special. He was growing tired of being with the middle-aged divorcees or overweight thirty-somethings. Rarely did any of these encounters result in anything more than a one night stand. His deepest desire was to find a woman who would willingly submit herself to his sexual fantasies. The only women that slept with him did so out of low self-esteem. However none were desperate enough to try anything too out of the box. He knew that finding his perfect woman would not be easy.

Wearing his usual robe that barely reached down far enough to cover his tiger print underwear, Quagmire walked into his yard to retrieve his local Quahog newspaper. On his way back he noticed an envelope taped to his front door. It was addressed to "Mr. Quagmire". He grabbed the envelope off of his door, and continued inside his bachelor pad. After placing the newspaper and envelope on his table, he jumped back into his round bed and wiggled under the covers. Being so tired from a night of boring meaningless sex, he lay in bed thinking about his perfect woman until he dozed off to sleep.

Quagmire awoke several hours later. He was having the most vivid dream about some of the things he wanted to try with his perfect woman. He was disappointed that his dream was interrupted, until he realized that it was already the mid-afternoon. He had always been grateful that his job as a pilot took him to the most exotic places and afforded him the flexibility in hours that allowed him to have a lifestyle where he had regular trysts with women, both domestically and abroad. Given the time, he decided that he'd better get up and moving, before another night of prowling for women.

In the shower he found himself reminiscing about his dream:

 _He remembered the tongue that teased the tip of his penis, and then his balls, and then back again, running along his shaft. Her soft and gentle hands knew just how to handle him as she prepared to devour his cock. Her warm and welcoming mouth was like a vacuum, the way it was sucking him in. Her soft hair was perfect for gripping as he shoved himself further down her throat, creating the most heavenly sound. She allowed him to place both hands around her neck as he firmly pressed around it. She was already oxygen deprived from his cock in her throat, but the strangulation was pushing both of them over the edge. When he felt like he couldn't make a single additional thrust without releasing his seed into her throat, he paused to pull out. To his delight, she grabbed him around the waist and continued to suck on his cock. She made eye contact, to let him know that she wanted him to release inside of her. He granted her wish, and his legs trembled as his orgasm overtook him. She gulped and gulped, making sure that his entire hot load made its way into her stomach. Before she was done, she made sure to clean his softening cock with her tongue. Finally finished, she lay next to him with a sly smile, knowing that they both were satisfied. Her own satisfaction came from satisfying Quagmire._

Suddenly pulled back into reality, Quagmire found himself ejaculating in his shower stall. His dream looked and felt so real, that he was totally immersed in it. He never even realized that his hand was rubbing his cock, let alone to completion.

After finishing his shower, Quagmire was certain of only one thing. He was done chasing after women that could never fulfill his sexual needs. He was going to find his perfect woman.


	2. Chapter 2 -- The Party

********This chapter doesn't contain any smut, but is integral to the story. Thank you to all of my readers. ********

Quagmire had gotten dressed in his usual red Hawaiian shirt with yellow flowers, jeans, and brown shoes. He felt a little relieved, knowing that he wasn't trying to impress anyone that night. There was no need to dapper up, because his perfect woman would accept him the way he was. His only concern was figuring out where he would be able to meet such a woman. Eventually it occurred to him to check his newspaper for events occurring around Quahog. He went to retrieve his newspaper from the table, when he saw the envelope that was addressed to him again. Curiously, he opened the envelope to examine its contents:

 _Dear Mr. Quagmire,_

 _You are casually invited to join my family in celebrating my 18th birthday. It's supposed to be a surprise party, but my dad is making me send out my own invitations after my mom asked him to do it. So I guess it's not really a surprise. The party will be held at 8PM tonight at our house. Feel free to show up any time. Gifts are not required, but always appreciated._

 _I hope to see you there,_

 _Meg_

Normally, the idea of spending his night at Meg's party would have been very unappealing. But, he wasn't currently preoccupied with finding a woman with hookup with. Perhaps Lois or Bonnie would know a nice woman that they could introduce him to. Maybe they would be unwilling to help him because of his track record with women. If he was serious about starting his quest for his perfect woman, attending Meg's lame party on a night that was usually reserved for prowling for women would be the perfect way to show everyone that he was ready for commitment.

After preparing and eating dinner, cleaning up and catching up on some TV, Quagmire headed over to the Griffin house. He arrived well after the party was supposed to have started, but upon entering the home, he found that he was the only guest that bothered to show up. Apparently Meg's family had given up on her party, and left her alone downstairs. She had been the one to answer the door and let him in.

"Oh, hi Mr. Quagmire. My dad is upstairs with my mom. I can get him for you if you're looking for him."

"Meg, I'm not looking for Peter. I came over for your birthday party. Speaking of which, Happy Birthday!" He handed her a small package that he had received in the mail. He assumed that it was the scarf that his mother knitted for him. He hadn't actually gotten around to opening it himself, but was in a hurry to find a present and get over to Meg's party.

"Thank you Mr. Quagmire! I'll put this over here, at my gift table". The table that she was referring to only had one other present on it. "I can open these after we eat cake. Let's go get some now." Quagmire followed Meg into the kitchen, where they found Brian, Chris, and Stewie finishing up the last few bites of what he presumed had been Meg's birthday cake. "You guys! What are my guests supposed to eat at my party?"

"What guests? Nobody likes you Meg! You couldn't even get Neil Goldman to come to your party!" Chris yelled at her.

"Listen Meg, we all know that no one was going to show up to your party. Chris, Stewie, and I were just getting rid of the cake so you didn't have to keep being reminded of this epic rejection. We were doing you a favor. You would've eaten this whole cake tonight, and you could stand to lose a few extra pounds anyways." Brian said, managing to sound like he was helping in between insults.

"Yeah Meg! You're such a cow! You'd better get out of here before the old man mistakes you for one and tries to turn you into a cheeseburger and eat you! MOO! MOO!" mocked Stewie.

Meg ran out of the kitchen crying, and retreated to her bedroom. Quagmire was still standing in the kitchen in shock. He'd never realized how truly horrible Meg's family, and everyone else for that matter, treated her. He knew how difficult it was to be misunderstood by the entire world. He decided that if he wasn't going to be bringing pleasure to some woman that night, he wanted to try and brighten Meg's spirits.

He left the kitchen and stopped by the gift table to grab the present he brought with him. The other had been addressed "To: Meg" and "From: Meg". He let out a sigh of disappointment before heading upstairs to Meg's room. He knocked on the door, but knew that she couldn't hear it through her loud crying. Quagmire opened her bedroom door and found her lying on her bed, weeping into her pillow. Slowly, he approached her bed before sitting on it. He placed his arm on her shoulder in an effort to comfort her.

"Hey there kiddo. The party tonight isn't such a big deal. Stuff like this happens all the time. Don't pay any attention to what those jerks said down there."

"No Mr. Quagmire. They're right. I'm just a huge loser and it's about time I accept that. Neil, the one guy that supposedly likes me, couldn't even be bothered to show up. I should just prepare myself for a lonely life, without any friends or family. I'd probably fail at being a cat lady because all the cats would run away or kill themselves. Please just leave me alone."

"You can't seriously believe that your life will turn out like that. I'm sure that the right guy, or girl, for you is out there somewhere. But you've got the rest of your life to worry about that. You should be celebrating today. Besides, the party isn't the best part about a birthday. The presents are. I have one for you right here. It's something that I believe will be very useful to you. Once you open it, I'll even model it for you."

After an audible **sniff, sniff** Meg turned to Quagmire, and took the gift out of his hands. As she began to open it, Quagmire got a small glimpse of the inside packaging. He could make out the word "Ring" and suddenly realized that he had made a grave mistake. He had placed an online order last week, and never expected to receive it this soon. It never occurred to him that the package would be anything other than a knitted scarf. But before he could do or say anything, Meg and finished opening her present.

"Uh… Mr. Quagmire?" Meg said hesitantly. "You gave me a cock ring?"


	3. Chapter 3 -- The Happy Accident

*******This chapter contains a lot of smut. Feel free to let me know what you think. As always, enjoy.*******

"Holy crap! I'm so sorry Meg! I never meant to give this to you! I thought it was a scarf that I was expecting in the mail!" Quagmire shouted as he jumped off of the bed. "This is so embarrassing. Here, hand it back to me and I'll get you a new present tomorrow."

"So does your offer to model it still stand in the meantime?" Meg asked attempting to sound seductive.

"Of course it doesn't Meg. You're my best friend's daughter. You're young and vulnerable right now. And I'm trying to be a better man."

Meg rose to her feet to look him straight in the eye as she desperately pleaded, "Please Mr. Quagmire! Please have sex with me! Who cares what anyone else thinks? And why do they have to even know for that matter? I'm 18 and old enough to make my own decisions. I'm through letting society dictate how miserable my life is. Today is my birthday and I should be doing something momentous to celebrate it. You said so yourself."

"Meg…I'm flattered that you want to sleep with me," Quagmire stammered. "But I really think that this is something you should be doing with boys your own age, not old Mr. Quagmire."

"You're not old, you're mature. Besides, boys my age don't even know the first thing about sex. I know that you've slept with plenty of women, so you should be experienced enough to make it special."

"Even if I agreed to have sex with you, it would be almost impossible to do it without anyone hearing us."

"Meg," an annoyed voice interrupted through the floor. It was Lois. "We're all going out to get some ice cream. Brian told us that your fat ass ate all of the birthday cake. That was really selfish of you, so you're not invited to come with us. You can just sit in your room and wallow in your self-pity. Oh, and stay away from the knives and razor blades. The last thing I want to do tonight is try to get blood stains out of the carpet." A door could be heard closing, and then the house was silent.

"Well, that's one problem solved," Meg said, sitting back down on the bed.

"Meg, are you 100% sure that you want to do this? Women always regret sleeping with me in the end."

"Mr. Quagmire, I'm very confident about this decision. Now please sit down on the bed with me and fulfill your promise to model my present," Meg ordered as she invitingly patted her bed with her hand.

Quagmire obliged her request and sat down next to her. She was busy trying to get the cock ring out of the box. He laughed in his head at her determination to open the packaging. She seemed so innocent, so eager. He took the box from her hands and had the cock ring out in seconds. She curiously examined her gift, and her confusion was evident.

"What do you say we start things off a bit slower? There's no need to jump right into sex," Quagmire offered.

After Meg nodded her head in agreement, Quagmire cupped her face with his hands and pulled her towards him so that they could lock lips. He was soft and gentle, starting off slow. She fell back, into her bed and he moved to be on top of her. Their bodies touched for the first time, and there was an instant reaction by both. Their pelvises started to grind together as their kissing became more fervent. He was surprised and pleased to find that they shared so much physical chemistry.

Quagmire pulled back to catch his breath and asked, "Meg, are you absolutely certain about this?"

"Absolutely!" Meg grabbed Quagmire's shirt and pulled him back down into her embrace as they locked lips once more.

His lips soon left hers as they ventured down to her neck. He knew that she was enjoying his handiwork, because he could hear her moans. Once satisfied with the work he'd done on her neck, he made his move down to her collar bone. Her shirt was in the way, so he roughly and wordlessly yanked it off above her head. He immediately started to work on undoing her bra, so that he could have complete access to her chest. All the while, his lips never left her body for more than a few seconds. As he sucked and lay butterfly kisses on her collar bone, she reciprocated by starting to unbutton his shirt. She longed to feel their chests pressed together, with direct skin to skin contact. Before she could finish unbuttoning the shirt, he took action by ripping it off.

Just as the red Hawaiian shirt, and a few broken off buttons, hit the carpet in Meg's bedroom, Quagmire moved back up to Meg's head and plunged his tongue into her mouth. At first she struggled, not knowing what to do with her own tongue. It didn't take long at all before their tongues were intertwined, and Quagmire had coaxed Meg's tongue into his own mouth. She could feel his throbbing member against her thigh. His hands moved to grab her breasts. They weren't the most firm he'd ever felt, but certainly not the saggiest. He began working on her nipples by flicking and gently pinching them. She reacted to his every touch by lightly moaning into his mouth.

He then traced down her neck with his mouth to her heaving chest. His mouth lightly sucked one nipple and then the other, while the other breast was caressed by his large, warm hands. Her reactions intensified as he used his tongue to circle around her areola and nip at her nipples. She was experiencing a new sensation that rippled through her body, and caused her underwear to dampen.

"Ooh Mr. Quagmire, keep going. This feels so good."

He was happy to oblige her as he moved down her chest, to her belly button. He unbuttoned her jeans, but found it difficult to get them off. Without needing to communicate, he stood to pull off his own pants and underwear in one motion, while she followed suit by removing her own. They paused to stare at each other's naked bodies. Quagmire could see that she carried a few extra pounds, but he was no stranger to hooking up with overweight women. Her young body was soft, and had much potential.

Meg was more shocked at what she saw. His body was lean and surprisingly fit for a man of his age. Most of his body was hairless, except for his chest. Perhaps the biggest shock of all to Meg was his penis, which was a respectable 7 ½ inches, but to her it was gigantic. She was growing more nervous by the second, as she stared at his swollen member in awe.

Noticing her strange response, Quagmire thrusted his pelvis in her direction and jokingly asked, "What's the matter, Meg? Haven't you seen a penis before?"

"Well of course I've seen a penis before…just not in real life," Meg answered as her cheeks blushed red.

"Jesus, Meg! Are you still a virgin?"

"Yes. What did you think I meant by asking you to help make my birthday special?"

"I thought you wanted me to be your first older man that had the experience that teenage boys lack."

"Well, you can be both."

"I don't know about this, Meg. I'm starting to rethink all of-"

Before he finished his sentence, Meg lunged towards Quagmire and grabbed his penis. He grimaced as she gripped it tightly, further showing her inexperience. She nervously began to move her hand up and down, along his shaft. It didn't take long before Quagmire had completely forgotten his train of thought. Her hand job skills were subpar, but with her every movement, he was coming closer to the point of no return. She left to grab the cock ring, while he stood motionless. It was stretched around her hand, as she slid it to the base of his cock. This additional level of sensitivity was too much to handle. His primal instincts kicked in, and he needed to find release.

He pushed her back down on the bed, before jumping on top of her. After moving down to her thighs, his hands spread her legs open, and he finally got a clear view of her vagina. Her brown bush was trimmed, but still seemed unkempt. Again, this was not a new experience for Quagmire. However, at this point, appearances did not matter. He was determined to fill her virgin hole, and it was killing him that he would have to go slow. But not too slow, because she was the one who had pushed him over the edge, and he would not take things easy on her.

He stuck his head between her thighs and watched her juices start to drip as his warm breath made contact with her. She jumped when his tongue grazed her sensitive nub. Her hands reached down to grip his hair as his tongue circled her swollen lips and sucked on her clit. When he could stand it no longer, his tongue hungrily delved into the depths of her vagina. He eagerly lapped up her juices and reveled in her cries of ecstasy.

Before she could reach her first orgasm, he moved back up to her head and she whimpered in disappointment. He lined his cock up to her entrance, and looked in her eyes with anticipation as he slowly moved forward until he reached her maidenhead. Her eyes were tightly closed and her face contorted in pain.

"Meg, look at me," Quagmire snapped.

She complied by opening her eyes, and he roughly thrusted forward, causing her to shriek in pain. With one thrust, his cock was fully sheathed by her warmth, and she struggled underneath him, trying to escape this discomfort. When she settled down, he started to rock back and forth, allowing her to adjust to his size. He would have waited for her to match his gentle rhythm, but she was just too tight. Before she was prepared, he picked things up by turning on the vibrating bullet on the top of the cock ring. She gripped his forearms that were placed on either side of her. His thrusts were slow, but deep, and his balls slapped her ass. Eventually her pain turned to painful pleasure, so she began to buck her hips to meet his thrusts, and she wrapped her legs around his waist. Their bodies writhed together wildly. The squeaks from her bed were in unison with their grunts. They were both so close to orgasm. Quagmire drilled into Meg without abandon. She was having difficulty keeping up with his rapid strokes, when a guttural moan escaped her throat. Her body convulsed while her walls constricted around his cock. Her already tight pussy was growing tighter, which caused him to groan as he reached orgasm. Her body milked his cock, and his hot cum spurted deep into her.

His arms gave out, and he collapsed on top of her. They were both too spent to move. As Quagmire regained his breath, he pulled his penis out of her, wiped it off with a nearby tissue, and took off the cock ring. He started to get redressed while she was still lying in bed, with a smile across her face.

"Mr. Quagmire, that was the best birthday present ever."

"Meg, I think you can just start calling me Glenn now."

"Alright…Glenn." Her eyelids were growing heavy as she tiredly said those last words. Exhaustion got the best of her, and she dozed off to sleep.

Quagmire looked up from buttoning his shirt, and saw her slumbering figure. She was still naked, and had pulled her sheet up to cover her breasts. She looked so peaceful in her afterglow. It had been years since Quagmire had helped a woman achieve that level of satisfaction. He felt gratified knowing that the only reason she felt that way was because of him. She was definitely a special girl, and maybe their encounter hadn't been so unpleasant after all. He knew that he wanted to see her again, so he quickly wrote her a letter to read in the morning, and left it on her bedside table. Quagmire walked out of her room and quietly shut the door, before exiting the Griffin house. All that he could do was head to bed, and wait for morning to find out her response to his letter.


End file.
